Vilsmeier cyclization of alpha-acetyl-alpha-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones

Yu Haifeng; Zhang Yongmei; Li Tiechun; Liao Peiqiu; Diao Quanping; Xin Guang; Meng Qingling; Hou Dongyan

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Vilsmeier cyclization of alpha-acetyl-alpha-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones

机译：Vilsmeierα-乙酰-α-芳酰基酮酮，S-缩醛的环化：直接高效合成卤化吡啶-2（1H） - 酮

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An efficient synthetic route to 3-aroyl-5-formyl-4-halo pyridin-2( 1H)-ones has been developed via Vilsmeier cyclization of 2-(ethylthio(arylamino) methylene)-1-alkylbutane-1,3-dione. The synthetic protocol has demonstrated the first example of Vilsmeier cyclization of alpha-acetyl-alpha-aroylketene-N,S-acetals, providing a novel route to 4-bromo/chloro pyridin-2(1H)-ones.

机译：通过Vilsmeier环化的2-（乙基氨基（芳基氨基）亚甲基丁烷-1,3-二酮的vilsmeier环化，开发了高效的合成途径-4-卤素-4-卤素吡啶-2（1H） - 。合成方案已经证明了α-乙酰基-α-芳炔-N，S-缩醛的vilsmeier环化的第一实例，提供了新的4-溴/氯吡啶-2（1H）-ONE的新途径。

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来源
《RSC Advances》 |2015年第15期|共4页
作者
Yu Haifeng; Zhang Yongmei; Li Tiechun; Liao Peiqiu; Diao Quanping; Xin Guang; Meng Qingling; Hou Dongyan;
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作者单位

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

NE Normal Univ Dept Chem Changchun 130024 Jilin Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

Anshan Normal Univ Sch Chem &

Life Sci Anshan 114007 Liaoning Peoples R China;

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正文语种 eng
中图分类化学;
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1. Vilsmeier cyclization of alpha-acetyl-alpha-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones [J] . Yu Haifeng, Zhang Yongmei, Li Tiechun, RSC Advances . 2015,第15期

机译：Vilsmeierα-乙酰-α-芳酰基酮酮，S-缩醛的环化：直接高效合成卤化吡啶-2（1H） - 酮
2. Efficient One-Pot Synthesis of 1,3-Disubstituted Pyridin-2(lH)-ones from a-Hydroxyketene S,S-Acetals under Vilsmeier Conditions [J] . Jim Liu, Deqiang Liang, Mang Wang, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2008,第22期

机译：在维尔斯迈尔条件下由α-羟基烯酮S，S-缩醛高效单锅合成1,3-二取代的Pyridin-2（1H）-one
3. A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones from α-oxoketene-S,S-acetals [J] . Yang X., Cheng Y., Zhao F., Tetrahedron . 2011,第43期

机译：从α-氧杂环丁烯-S，S-缩醛轻松高效地合成全取代的pyridin-2（1H）-one
4. Efficient Synthesis of 3, 4-Dihydropyrimidin-2(1H)-Ketone Using SbCl_3 as Catalyst under Ultrasonic Conditions [C] . Jin Lin, Jing fen Li, BinbinZheng, International Conference on Energy Engineering and Environmental Engineering . 2013

机译：在超声波条件下，高效合成3,4-二氢嘧啶-2（1H） - 酮作为催化剂的SBCl_3
5. 1. Application of the intramolecular crossed [2 + 2] photocycloaddition/retro-Mannich/Mannich cascade of vinylogous imides toward the synthesis of a sarain A bicycle. 2. Studies directed toward the synthesis of nakadomarin A [D] . Fitzgerald, Mark E. 2008

机译：1.分子内交叉的[2 + 2]光环加成反应/乙烯基乙烯基酰亚胺的复古-曼尼希/曼尼希级联在萨兰A自行车合成中的应用。 2.研究nakadomarin A的合成
6. Design Synthesis and Biological Activity of 46-disubstituted Pyridin-2(1H)-ones as Novel Inhibitors of Soluble Epoxide Hydrolase [O] . Leila Hejazi, Elham Rezaee, Sayyed Abbas Tabatabai 2019

机译：46-二取代的Pyridin-2（1H）-ones作为新型可溶性环氧水解酶抑制剂的设计合成及生物活性
7. Efficient One-Pot Synthesis of Highly Substituted Pyridin-2(1H)-ones via the Vilsmeier-Haack Reaction of 1-Acetyl,1-Carbamoyl Cyclopropanes [O] . -1

机译：通过1-乙酰基，1-氨基甲酰基环丙烷的Vilsmeier-Haack反应有效地合成高度取代的吡啶-2（1H） - 酮 - 丙酮烷基反应

Vilsmeier cyclization of alpha-acetyl-alpha-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones

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